Process for the manufacture of para tertiary butyl aniline



Patented Sept. 14, 1937 UNITED STATES PATENT OFFICE PROCESS FOR THEMANUFACTURE OF PARA TERTIARY BUTYL ANILINE Bernard Herstein, Brooklyn,N. Y., assignor to U. S. Industrial Alcohol 00., New York, N. Y., acorporation of West Virginia 1 Claim. (Cl. 260-1305) This application isa division of application Serial No. 46,123, filed October 22, 1935.

The object of the invention claimed herein is to provide a simple andeconomical way of manufacturing para tertiary butyl aniline, a compoundwhich is suitable for purposes similar to those for which para-toluidineis used, for the production of compounds of the same general characterbut with some specific properties of their own.

The following example illustrates the preferred mode of operation. Theparts of ingredients will be understood to be parts by weight.

34 parts acetanilid are suspended. in 85 parts ethylene dichloride and40 parts anhydrous aluminum chloride are added. The temperature tends torise but by cooling is not permitted to go above 50 C. When all but avery small amount of aluminum chloride is in solution the reactionmixture is cooled to 10 C. and 25.2 parts tertiary butyl chloride added.The temperature is maintained at about 5 C. for 30 minutes. At thistemperature, the evolution of hydrochloric acid gas is not vigorous andthe reaction may be maintained at that temperature at which theevolution of HCl is just visible from the surface of the reactionmixture.

This is then poured cautiously into 250 parts of cracked ice by whichthe intermediate complex of aluminum chloride and the organic com poundis decomposed by the water and the aluminum chloride goes into solutionwhile the p-tertiary butyl acetanilid and ethylene dichloride form adoughy mass or solution which is removed and washed two or three timeswith fresh water to leach out as much inorganic material as possible.The solvent ethylene dichloride is then removed either by steamdistillation or other convenient method. This leaves the product, paratertiary butyl acetanilid, behind in the form of a crystalline masswhich may be filtered and washed and subsequently dried. The averageweight of the material thus obtained is 45-46 parts. The material may befurther purified if desired, though a higher degree of purity is notrequired for most purposes.

From the para tertiary butyl acetanilid thus i hydrous aluminumchloride, obtaining from the' reacted mixture para tertiary butylacetanilid, and deacetylating this material to obtain para tertiarybutyl aniline.

BERNARD HERSTEIN.

